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Story: The Christmas Bet

I run my hand through my hair. I let out a long breath and look at him. “Do you have any idea how hard this is? I feel like absolute shit about all of this. I’m using her for my own personal gain.”
“Well, I mean last night it worked out in your favor. Got yourself a taste.” Roland shrugs nonchalantly.
“How the fuck are you even married?” My eyes narrow at him. “This is apersonwe are talking about. Someone with feelings.”
“First, my wife loves me, and I love her. Second, I’m not saying you have to marry the woman, but you are actually committing yourself to her for all this. It’s not as if you’re off and screwing around while dating her. So, I mean, really, you’re in a dating relationship. You know, the real thing.”
“The guilt is eating away at me. Last night,”—I run my hands over my face—“she was laying there after, and that’s when it fucking hit me. She’s beautiful, she’s funny, she’s everything. But I don’t want that. I don’t want a ball and chain. But I’m leading her on to think that I do. When I eventually pull back, when I end it … I’ll end up hurting her.”
“Wow, Jack was right. You might be the first lawyer with a conscience,” he replies with a laugh.
“Shut the fuck up, asshole. It’s called being a decent human being, something you are apparently not familiar with. This bet? This bet is the most selfish, in-humane, stupid as fuck thing to do to someone.”
“You agreed to it. You went in on the bet.”
“I know. I know. Fuck!” I jump out of my chair and walk towards the window. “I haven’t slept well since I left her apartment.”
“So, you want to throw in the towel? You know what you’re giving up, so that’s on you.” Roland lets out a little chuckle. He’d keep his 1969 Mustang Mach 1, so he would love for me to back out. “Beth would be devastated to know that the Mustang is staying with us. She’s been wanting it gone forever.”
Ugh. The twisting in my stomach tightens. “I don’t want to throw in the towel. This is killing me inside, and I know when I break it off with her, she will hate me with every bone in her body. That kills me even more.”
“Why do you care? If you aren’t looking for love, then just do what you need to so you can get through this. It doesn’t have to end in an actual marriage; she just needs to want to marry you. It’s simple. Again, why would you care?” Roland crosses his leg over his knee and throws me a puzzling look.
“How the fuck did you actually find a woman to even put up with your bullshit? Fuck, I need to get Beth an all-expense trip to Europe or something just for marrying you. You’re a complete assfuck.” I shake my head, completely blown away at how my friend is pushing me to go through with this. This is not the man I grew up with. I don’t know if it’s him wanting me to actually fail or what, but he’s not acting himself. Our bets never hurt or threatened to hurt anyone outside of our group.
Roland uncrosses his legs and leans forward. “You feel something for this chick, don’t you?”
“Her name is Allison,” I growl. “And I don’t know what I feel.”
Except that I do. Sort of. I know that my body seems to respond when I’m around her or even thinking about her. I love the smell of her shampoo. And I wanted nothing more than to slide inside her and feel her warm pussy wrapped around my cock. Fuck, and now I’m starting to sport a hard on just thinking about it.
“Look, I need to get some work done. See yourself out, would you?” I ask.
Roland innocently holds up his hands. “Fine. Fine. I’ll go. Should I tell the guys you’re backing out?”
“Get out!”I yell.
Roland laughs as he leaves my office and I return to my desk, sighing, not sure what I’m going to do. I haven’t talked to her since I left, and now I’m not sure if I should or if I should just let it fall out and move on with my life.But then I’ll lose the bet.
It’s not like I don’t have enough to do as it is. My clients depend on me.This job takes up a lot of my time and focus.
“Mr. Dawson.” My assistant’s voice breaks through the intercom on my phone, interrupting my thoughts. “Your mother is on the line. Would you like me to put her through?”
The fog clears out of my head. “Yes, please.” I pick up the phone just as my mother gets sent through.
“Hi, my boy. How are you doing?” My mother’s cheery voice filters through the phone receiver.
“Hi, Ma. I’m fine. How are you?” My tone is flat, which I internally curse myself for because she will pick up on it.
“What’s wrong?” There it is. Now she’s all worried.
“Nothing. Just stressed out with work. I have a lot of things going on.”
“You work too hard, my boy. You need to get out. Date some ladies, experience a social life.”
“I have a social life. I have the guys and I talk to you, don’t I?” I laugh dryly.
“Conner, sweetheart, as much as I love you, I’m not your social life. You need a good woman in your life. Someone to make you smile, to fall in love with. And of course, most importantly, make me some grand-babies to love on.”